Synthesis of 2-methyl-4-selenoquinazolone, 2-phenylbenzoselenazole, and its derivatives: Dissertation submitted in partial fulfillment of the requirements for the degree of Doctor of Philosophy in the Faculty of Pure Science of Columbia UniversityChen, Yü-Gwan
Science
Synthesis of 2-methyl-4-selenoquinazolone, 2-phenylbenzoselenazole, and its derivatives: Dissertation submitted in partial fulfillment of the requirements for the degree of Doctor of Philosophy in the Faculty of Pure Science of Columbia University
Chen, Yü-Gwan
Organic compounds -- Synthesis; Selenium; Thesis (Ph. D.)
Sulphides and disulphides have curative power. Dimethylsulphide is
used for internal treatment, di-o-aminophenyldisulphide is used for
intramuscular injections. Diallyl sulphide is also a medicament.
Methyl selenide has some effect on the internal parts of the body(33).
Hanzlik and Tarr(34) at the American University Experimental Station,
showed that a number of selenium compounds act as skin irritants: e.g.,
dichlorodiethyl selenide, dichlorovinyl selenide, trichlorodiethyl
selenide and selenium mustard oil. The first mentioned proved as potent
as the sulphide, but the others fell somewhat below in their effects.
Diantipyryl selenide is another therapeutical agent(35).
The diselenides occupy an important place of their own. The
selenophenols do not remain unchanged in the air, but are always
oxidized to the diselenides, which can be again reduced to the
selenophenols. So far only the diselenides of anthraquinone and their
phenols are recognized remedies(36).
TINCTORIAL REVIEW
Many of the seleno organic compounds are colored, while the
corresponding sulphur derivatives are colorless.
HC-CH HC-CH
|| || || ||
HC CH HC CH
\ / \ /
O S
Furane, colorless Thiophene, colorless
liquid liquid
HC--CH HC--CH
|| || || ||
HC CH HC CH
\ / \ /
NH Se
Pyrrol, colorless liq. Selenophene, yellow liq.
but turns brownish in air after repeated extraction[B]
This brings selenophene more akin to pyrrole than thiophene, but the
group -NH- in the molecule of pyrrole is an auxochrome. The selenium
atom in a cyclic compound also acts like an auxochrome.
Selenoantipyrine(37),
C₆H₅
N
/ \
CH₃N CSe
| |
CH₃C===CH
forms pure yellow crystals from alcohol, while the corresponding
compounds of oxygen and sulphur are colorless.
Similarly, the 2-methyl-4-selenoquinazolone is deep brown in color,
while the thio compound, prepared by Bogert and Hand(38) is light brown
or yellow and the corresponding oxygen compound is colorless or nearly
so.
Diethyl selenide (C₂H₅)₂Se, is a yellowish heavy oil of unpleasant odor.
It combines readily with chlorine to form a chloride (C₂H₅)₂SeCl₂, and
the latter is oxidized by nitric acid to form an oxide (C₂H₅)₂SeO,(39).
Diethyl sulphide is a colorless syrupy liquid, as well as diethyl amine
and diethyl ether.
The gradation of color is quite pronounced in the case of
selenonaphthene quinone(40).
CO CO CO CO
/\ / \ /\ / \ /\ / \ /\ / \
| | CO | | CO | | CO | | CO
\/ \ / \/ \ / \/ \ / \/ \ /
O S NH Se
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